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The Rules of Prep: Newbie Edition


Preppy fashion often gets a bad rap for being too high brow. And it’s truly no surprise. After all, it was the de facto school uniform of Ivy-league universities in the 20th century; the style’s aesthetic derived from high-brow sports like eq and yachting; and it basically defines America’s contemporary upper and upper-middle class.

Despite its privileged origins, the preppy style really is for everyone. It flatters any profile, is easily adopted, and earns instant respect from those willing to ignore the derisive opinions of the uninitiated.

If you’re looking to adopt the style as your own, consider this your crash course in the basic principles of contemporary prep.

The Ground Rules....

Dare to Be Different

Many lifelong prep adherents will deny that their style is conformist, but between you and me, it has that strong tendency. Don’t let yourself fall into the trap of doing what every other prepster out there does: give your shoes some colorful laces; let your tattoo show, even just a little bit; invest in a quirky yet colorful pair of socks. The last thing you want to do is blend into the crowd.

Just Do You

Since we’re talking about being different, remember one thing (as cliche as it will sound): you are different. However you decide to spice up your outfit, don’t do something that doesn’t feel right. For example, never wear a sweater from a school you never attended. Embarrassing conversations are bound to follow. This also means steering clear of attire alluding to past-times you don’t partake in. For example, never invest in sailing clothes if you don’t actually go sailing.

Strive Against Douchebaggery

I’ve seen this one way too many times: someone adopts the preppy aesthetic, and they turn into a douchebag. They sneer at their friends for drinking beer instead of a cocktail and look down on their pals for wearing gym clothes in public. But you know what’s my absolute favorite? When the new prep decides to pop his shirt collar. In summary, never act like a douchebag or look like one.

Invest in Quality

I get it, we all have our budgets. Nevertheless, getting the preppy look right means investing in quality garments. Brightly colored pants or shirts generally aren’t preppy if they’re cheaply priced and made with less-than-stellar materials. And, of course, if you’re going for a vintage look, invest in real vintage. Pre-aged anything will become even more worn out over time, making them unusable for your preppy look. Not to mention that pre-aged anything is a dime-a-dozen. You’ll totally blend in…which is not what we’re going for, remember?

Be Functional

Yes, preppy clothes tend to run on the expensive side. They are, after all, made with heavy weight cotton, wool, and linen. Remind yourself that it’s worth it. Aside from making a major investment in your style, you’re buying cloths that are built to last. And, of course, never forget the words of wisdom given to us by Lisa Birnbach, the author of The Official Preppy Handbook:

Prep clothes are sensible: rain clothes keep you dry; winter clothes keep you warm; collars are buttoned down so they dont flap in your face when youre playing polo. Layering is a natural response to varying weather conditions.

Parting Thoughts

You now have the basic rules that will serve as the groundwork to a successful prepster outfit. Tailor Vintage has you covered…and you know this!


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